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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:34 UTC
HMDB IDHMDB0059611
Secondary Accession Numbers
  • HMDB59611
Metabolite Identification
Common NameThiomorpholine 3-carboxylate
DescriptionThiomorpholine 3-carboxylate, also known as 3-thiomorpholinecarboxylic acid or 1,4-tmca, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Thiomorpholine 3-carboxylate is a very strong basic compound (based on its pKa). A thiomorpholinemonocarboxylic acid having the carboxy group at the 3-position.
Structure
Data?1563865955
Synonyms
ValueSource
1,4-Thiomorpholine-3-carboxylic acidChEBI
3-Thiomorpholinecarboxylic acidChEBI
1,4-Thiomorpholine-3-carboxylateGenerator
3-ThiomorpholinecarboxylateGenerator
Thiomorpholine 3-carboxylic acidGenerator
Thiomorpholine-3-carboxylateHMDB
1,4-TMCAHMDB
Thiomorpholine 3-carboxylateChEBI
Chemical FormulaC5H9NO2S
Average Molecular Weight147.195
Monoisotopic Molecular Weight147.035399227
IUPAC Namethiomorpholine-3-carboxylic acid
Traditional Namethiomorpholine 3-carboxylate
CAS Registry NumberNot Available
SMILES
OC(=O)C1CSCCN1
InChI Identifier
InChI=1S/C5H9NO2S/c7-5(8)4-3-9-2-1-6-4/h4,6H,1-3H2,(H,7,8)
InChI KeyJOKIQGQOKXGHDV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Thiomorpholine-3-carboxylic acid
  • 1,4-thiazinane
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Thioether
  • Dialkylthioether
  • Organoheterocyclic compound
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility54.2 g/LALOGPS
logP-2.2ALOGPS
logP-2.6ChemAxon
logS-0.43ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.88 m³·mol⁻¹ChemAxon
Polarizability14.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.81931661259
DarkChem[M-H]-121.99231661259
DeepCCS[M+H]+126.18430932474
DeepCCS[M-H]-122.57630932474
DeepCCS[M-2H]-159.6130932474
DeepCCS[M+Na]+134.8530932474
AllCCS[M+H]+130.432859911
AllCCS[M+H-H2O]+125.932859911
AllCCS[M+NH4]+134.632859911
AllCCS[M+Na]+135.832859911
AllCCS[M-H]-129.932859911
AllCCS[M+Na-2H]-132.132859911
AllCCS[M+HCOO]-134.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Thiomorpholine 3-carboxylateOC(=O)C1CSCCN12221.9Standard polar33892256
Thiomorpholine 3-carboxylateOC(=O)C1CSCCN11285.7Standard non polar33892256
Thiomorpholine 3-carboxylateOC(=O)C1CSCCN11414.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thiomorpholine 3-carboxylate,1TMS,isomer #1C[Si](C)(C)OC(=O)C1CSCCN11410.0Semi standard non polar33892256
Thiomorpholine 3-carboxylate,1TMS,isomer #2C[Si](C)(C)N1CCSCC1C(=O)O1509.9Semi standard non polar33892256
Thiomorpholine 3-carboxylate,2TMS,isomer #1C[Si](C)(C)OC(=O)C1CSCCN1[Si](C)(C)C1544.4Semi standard non polar33892256
Thiomorpholine 3-carboxylate,2TMS,isomer #1C[Si](C)(C)OC(=O)C1CSCCN1[Si](C)(C)C1489.2Standard non polar33892256
Thiomorpholine 3-carboxylate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CSCCN11649.4Semi standard non polar33892256
Thiomorpholine 3-carboxylate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1CCSCC1C(=O)O1758.1Semi standard non polar33892256
Thiomorpholine 3-carboxylate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CSCCN1[Si](C)(C)C(C)(C)C2021.6Semi standard non polar33892256
Thiomorpholine 3-carboxylate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CSCCN1[Si](C)(C)C(C)(C)C1909.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thiomorpholine 3-carboxylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-5a061da8b9fdd6ce556d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiomorpholine 3-carboxylate GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-7900000000-373fa15eaf7160659de62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiomorpholine 3-carboxylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 10V, Positive-QTOFsplash10-000t-0900000000-4a4dacff869db8e934612017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 20V, Positive-QTOFsplash10-0uea-3900000000-e3220fe85d29a5cf8ded2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 40V, Positive-QTOFsplash10-03di-9000000000-204108b26436ef4d606c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 10V, Negative-QTOFsplash10-0002-1900000000-9cb3304443d6054f9e152017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 20V, Negative-QTOFsplash10-0006-9600000000-cfc569cb0b5f22d4fbe52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 40V, Negative-QTOFsplash10-0a59-9000000000-52f8c15caf0d453a6bf42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 10V, Positive-QTOFsplash10-0002-0900000000-a4b5527b99788d605c0a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 20V, Positive-QTOFsplash10-0zfs-5900000000-a1af266b87e9f0b7fe9d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 40V, Positive-QTOFsplash10-0abd-9100000000-0393bb000aca28ca661c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 10V, Negative-QTOFsplash10-0002-1900000000-7023d534d72b4e6053cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 20V, Negative-QTOFsplash10-0005-9600000000-791ad76b41dc2bca261f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiomorpholine 3-carboxylate 40V, Negative-QTOFsplash10-001i-9000000000-79b40c7d73b7271832c92021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03901
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440159
PDB IDNot Available
ChEBI ID17195
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Not Available
Specific function:
Specifically catalyzes the reduction of imine bonds in brain substrates that may include cystathionine ketimine (CysK) and lanthionine ketimine (LK). Binds thyroid hormone which is a strong reversible inhibitor. Presumably involved in the regulation of the free intracellular concentration of triiodothyronine and access to its nuclear receptors.
Gene Name:
CRYM
Uniprot ID:
Q14894
Molecular weight:
29425.425
Reactions
Thiomorpholine 3-carboxylate + NAD(P)(+) → 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)Hdetails